US4589921A - Process for improving the application properties of pigment yellow 13 - Google Patents
Process for improving the application properties of pigment yellow 13 Download PDFInfo
- Publication number
- US4589921A US4589921A US06/743,270 US74327085A US4589921A US 4589921 A US4589921 A US 4589921A US 74327085 A US74327085 A US 74327085A US 4589921 A US4589921 A US 4589921A
- Authority
- US
- United States
- Prior art keywords
- pigment
- suspension
- pigment yellow
- yellow
- coupling
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 5
- 239000000725 suspension Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims description 3
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000001052 yellow pigment Substances 0.000 abstract description 4
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 abstract description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000976 ink Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ULVDMKRXBIKOMK-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2,3-dihydroisoindol-1-one Chemical class ClC1=C(Cl)C(Cl)=C2CNC(=O)C2=C1Cl ULVDMKRXBIKOMK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 1
- HZEWFHLRYVTOIW-UHFFFAOYSA-N [Ti].[Ni] Chemical compound [Ti].[Ni] HZEWFHLRYVTOIW-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910001000 nickel titanium Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
Definitions
- 4,204,871 advises preparing azo pigments by mixed coupling in the presence of highly dispersed inorganic materials such as iron oxide, titanium dioxide, barium sulfate, aluminum hydroxide, clays or mixtures thereof to bring about an intimate bond between the inorganic material and the organic pigment mixture.
- highly dispersed inorganic materials such as iron oxide, titanium dioxide, barium sulfate, aluminum hydroxide, clays or mixtures thereof to bring about an intimate bond between the inorganic material and the organic pigment mixture.
- the invention therefore relates to a process for improving the application properties of Pigment Yellow 13, which process comprises heating the crude pigment in an aqueous suspension to temperatures above 100° C.
- an isolated and, if necessary, washed crude pigment can be dispersed in water, if desired with the addition of a surfactant, but preferably the coupling suspension obtained after the reaction of bis-diazotized 3,3'-dichlorobenzidine with finely divided 1-acetoacetylamino-2,4-dimethylbenzene, optionally in the presence of a surfactant, is used for the aftertreatment according to the invention.
- the pigment concentration of the suspension is advantageously 1 to 10, preferably 2 to 8, % by weight.
- the thermal aftertreatment is carried out with thorough mixing advantageously directly in the reaction vessel in which the azo coupling was carried out.
- the duration of the thermal aftertreatment depends on the temperature, which, in turn, is dependent on the pressure. Since elevated operating pressures require correspondingly expensive pressure vessels, the suspension is advantageously heated with thorough stirring to about 120° to 150° C. This treatment takes about half an hour to 5 hours.
- the treatment according to the invention leads to a pigment which, in viscosity behavior, in hiding power and in gloss, is surprisingly comparable with a product after-treated in an aqueous-organic medium in accordance with U.S. Pat. Nos. 4,048,152 and 3,974,136.
- the process according to the invention is distinguished by particular simplicity, since no organic solvent has to be used and regenerated.
- a bis-diazonium salt solution containing sulfuric acid and obtained from 25.3 parts of 3,3'-dichlorobenzidine was allowed, at 20° to 25° C., to flow into a finely divided acetate-buffered slurry of 42.1 parts of 1-acetoacetyl-amino-2,4-dimethylbenzene in 600 parts of water.
- the pigment suspension was heated to 125° C. in a stirred autoclave and maintained for 4 hours at this temperature. After the suspension had cooled down to 70° C., the pigment was filtered off, washed until salt-free, dried and milled.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813128057 DE3128057A1 (de) | 1981-07-16 | 1981-07-16 | Verfahren zur verbesserung der anwendungstechnischen eigenschaften von pigment yellow 13 |
| DE3128057 | 1981-07-16 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06614718 Continuation | 1984-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4589921A true US4589921A (en) | 1986-05-20 |
Family
ID=6137021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/743,270 Expired - Fee Related US4589921A (en) | 1981-07-16 | 1985-06-10 | Process for improving the application properties of pigment yellow 13 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4589921A (fr) |
| EP (1) | EP0070490B1 (fr) |
| JP (1) | JPS5819364A (fr) |
| KR (1) | KR880002513B1 (fr) |
| AU (1) | AU547031B2 (fr) |
| BR (1) | BR8204118A (fr) |
| CA (1) | CA1182113A (fr) |
| DE (2) | DE3128057A1 (fr) |
| DK (1) | DK152583C (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021090A (en) * | 1989-05-23 | 1991-06-04 | Sun Chemical Corporation | Water-based diarylide pigment compositions |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1003999A3 (fr) * | 1990-03-14 | 1992-09-08 | Colour Res Company Coreco Ltd | Pigments organiques ameliores, procede pour leur preparation et utilisation dans les peintures. |
| US5863459A (en) * | 1997-05-09 | 1999-01-26 | Sun Chemical Corporation | Fluorescent yellow azo pigments |
| CN105670333A (zh) * | 2016-01-14 | 2016-06-15 | 上虞大新色彩化工有限公司 | 一种c.i.颜料黄13的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469515A (en) * | 1979-07-11 | 1984-09-04 | Ciba-Geigy Corporation | Production of pigments |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH350746A (de) * | 1956-07-20 | 1960-12-15 | Ciba Geigy | Verfahren zur Herstellung von Farbpigmenten in leicht verteilbarer Form |
| CH407170A (de) * | 1960-05-28 | 1966-02-15 | Hoechst Ag | Verfahren zur Herstellung von Azopigmenten mit verbesserter Fliessbarkeit |
| DE2059675C3 (de) * | 1970-12-04 | 1974-04-11 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Verbesserung der anwendungstechnischen Eigenschaften eines Disazopigmentes |
| US3991044A (en) * | 1972-09-26 | 1976-11-09 | Hercules Incorporated | Process for improving lightfastness of an azo pigment by heat treatment |
| DE2302509B2 (de) * | 1973-01-19 | 1975-01-09 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Disazopigment, Verfahren zu seiner Herstellung und seine Verwendung |
| DE2302481B2 (de) * | 1973-01-19 | 1975-01-02 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Disazopigment, Verfahren zu seiner Herstellung und seiner Verwendung |
| DE2410730B2 (de) * | 1973-03-16 | 1976-09-09 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Thermoplastische strassenmarkierungsfarbe |
-
1981
- 1981-07-16 DE DE19813128057 patent/DE3128057A1/de not_active Withdrawn
-
1982
- 1982-07-12 DE DE8282106219T patent/DE3262657D1/de not_active Expired
- 1982-07-12 EP EP82106219A patent/EP0070490B1/fr not_active Expired
- 1982-07-14 KR KR8203132A patent/KR880002513B1/ko not_active Expired
- 1982-07-15 JP JP57122255A patent/JPS5819364A/ja active Pending
- 1982-07-15 DK DK318882A patent/DK152583C/da active
- 1982-07-15 AU AU86060/82A patent/AU547031B2/en not_active Ceased
- 1982-07-15 CA CA000407388A patent/CA1182113A/fr not_active Expired
- 1982-07-15 BR BR8204118A patent/BR8204118A/pt unknown
-
1985
- 1985-06-10 US US06/743,270 patent/US4589921A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469515A (en) * | 1979-07-11 | 1984-09-04 | Ciba-Geigy Corporation | Production of pigments |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021090A (en) * | 1989-05-23 | 1991-06-04 | Sun Chemical Corporation | Water-based diarylide pigment compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1182113A (fr) | 1985-02-05 |
| DK152583C (da) | 1988-09-19 |
| DK152583B (da) | 1988-03-21 |
| DE3262657D1 (en) | 1985-04-25 |
| DK318882A (da) | 1983-01-17 |
| KR880002513B1 (ko) | 1988-11-26 |
| DE3128057A1 (de) | 1983-02-03 |
| KR840000619A (ko) | 1984-02-25 |
| AU547031B2 (en) | 1985-10-03 |
| AU8606082A (en) | 1983-01-20 |
| JPS5819364A (ja) | 1983-02-04 |
| EP0070490A1 (fr) | 1983-01-26 |
| EP0070490B1 (fr) | 1985-03-20 |
| BR8204118A (pt) | 1983-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| AS | Assignment |
Owner name: HOECHST AKTIENGESELLSCHAFT, D-6230 FRANKFURT AM MA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:HUNGER, KLAUS;RIEPER, WOLFGANG;REEL/FRAME:004497/0618 Effective date: 19860107 |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| REMI | Maintenance fee reminder mailed | ||
| REMI | Maintenance fee reminder mailed | ||
| LAPS | Lapse for failure to pay maintenance fees | ||
| FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19940522 |
|
| STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |